Middle
Kloe (Legend of Heroes: Trails in the Sky) vs El Jackson (Wild ARMs XF)
Uh. DHE's notes on El Jackson is that he didn't test Misery? If El Jackson immunes it he wins, if he doesn't he loses. Tiebreaking against him mostly because if he resists Misery, he still probably loses - Kloe can go Anti-Sept -> Radiant Plash if it misses -> 2nd Anti-Sept attempt before losing, so she has two shots of a base 100% hit rate, so it'd have to be a heck of a good resistance.
Light
Andre (Shadow Hearts: Covenant) vs Kain Highwind (Final Fantasy IV)
Blood Spear? Unless Andre can surge his damage...
Olivya Phoraena (Tactics Ogre: Let Us Cling Together) vs Melody Vilente (Wild ARMs 3)
Melody's damage is MAGICAL. And is exactly a 4HKO according to Meeple's numbers. Olivya's healing can basically keep up with 4HKOs by default, and she's 6HKO'd by magic or something. She's only ever inflicting damage off Wrathful Strikes, but those may turn off Melody's counters, and it may not matter anyway - she can wait until she has a bit of spare MP in the tank before Wrathful Striking, then cure the poison, then resume healing. It's possible the Wrathful Strikes fail to break the barrier, I guess, but, eh. Takes years but think this is Olivya's.